A Thief's Guide to Stealing Back a Kingdom
by Londonvetgirl25
Summary: What if Sly wasn't sent to ancient Egypt but to another world entirely? He certainly didn't expect to wake up in a hole in the ground belonging to a certain hobbit. A hobbit who has never stolen a thing and may need a hand. And a cane. Can Sly survive Middle Earth and return home or will a certain group of dwarves and a wizard drive him insane first?
1. Prologue

Hey Guys, this is just an idea I have had for a long time now. Since Bilbo is hired to be a thief, wouldn't it be helpful to have an actual thief help out?

Disclaimer: I do not own anything from The Hobbit (which belongs to the great J.R.R Tolkien) or the Sly Cooper series (which belongs to Sanzaru/Sony). I only own this plot (well the plot areas not shown in the Hobbit movie) and a lot of student debt

And as always, please read & review (Please check out my other story if you have a moment).

Bilbo loved sunny mornings in the Shire. The rolling hills of green always provided a certain sense of peace in abundance, particularly while one enjoyed a good smoke of old Toby from their favorite pipe. Practicing his smoke rings, he began to plan what cakes to bake for the annual Conkers tournament the following day when his musing were cut off with a sudden flash of bright light. Dropping his pipe and rubbing his eyes, he opened them to an extraordinary sight.

On the ground in front of him lay perhaps the most peculiar creature he had ever seen. It looked like a raccoon. But, Bilbo thought wildly to himself, raccoons don't wear clothes, do they? And what is that strange stick he is holding onto? Edging closer, he heard the raccoon _begin to mumble_. "Carmelita... Carmelita" the raccoon groaned. By this point, Bilbo had come to the obvious conclusion that this was no ordinary raccoon and, being a kindly creature, got the Old Gaffer's help in bringing him inside.

* * *

Sly woke up slowly at first, then jolted awake, remembering the fight with Le Paradox and his involuntary trip through time. Seeing as he wasn't under attack he began to look around. He did not expect what he found. He found that he was in a hole in the ground. Not a nasty, dirty wet hole with the ends of worms and an oozy smell, nor yet a dry, bare sandy hole. This hole seemed to define _comfort_. He was lying on a soft bed that stood next to a window where he beheld rolling green hills, similar to those he had seen in medieval England. There was a roaring fire in the hearth (thought it seemed pleasantly warm outside) and the walls were covered in fine wood paneling.

Just then, a small creature bustled in with a tray of food which he set down a nearby table. Sly could only stare because he had never seen a creature like this before. Small, perhaps only three feet in height, with fur only present in patches which included his head and the tops of his feet, this creature, Sly guessed, must be some kind of small ape. Then the creature spoke.

"Good day sir. You were passed out on my front lawn this morning and you seemed in quite a bit of trouble so I brought you inside for a bit of rest" he babbled, clearly nervous. "If it isn't too rude of me to ask, may I ask who you are (not to mention what, but this was left unsaid) and how you managed to get here?"

Sly suddenly realized he was staring and quickly introduced himself. "My name is Sly. Sly Cooper. As to how I got here, I am not sure where here is."

"Oh" said Bilbo, "You are in Bag End in the Shire."

"I am sorry but I don't know where that is. I am from Paris."

"I have never heard of this Paris I am sorry to say. Oh, where are my manners? I am Bilbo Baggins of Bag End."

Sly hesitated, "This might sound really rude, but _what_ are you? I've never seen anyone like you?" Surprised, Bilbo answered, "Why I am a hobbit. Generally known as small folk or halflings which you may have heard" he added questioningly. When the raccoon shook his head Bilbo sighed "Oh well."

"Is it quite alright if I ask the same question of you sir?" Bilbo timidly ventured.

"Of course. I am a raccoon and a master thief" He said this last part with great pride. Seeing Bilbo stiffen, he hastily added "I only steal from bad guys."

"Well" Bilbo said, if a little stiffly, "If you would like, I have some tea outside if you would like some fresh air."

Acquiescing, Sly joined Bilbo outside, ducking his head to avoid hitting it as it was a little sore from his trip through the time vortex. Once there, Sly began to tell Bilbo all about his world, his family's legacy, his gang and his previous adventures. While Bilbo had been a little miffed at letting a thief into his home (what would the neighbors say when they heard?) he couldn't help but relax around the charming thief and, despite himself, become interested in his adventures.

When Sly was done talking, Bilbo remarked, "I must say these are extraordinary tales. I must also say that you may have landed in the one place where adventures are not exactly approved. They simply make one late for dinner. While you are here, would you like to stay here in Bag End? I am afraid that the Inn may not be as interested in your tales."

Sly answered, "Adventures are relatively routine for me. And that would be great, thank you."

Before either could say anything else, a tall man in a grey cloak and with a long staff appeared out of nowhere in front of Bilbo's house, staring intently at the unlikely pair.

* * *

"Good Morning" said Bilbo. He was beginning to feel that this was going to be a very strange day. The old man gave Bilbo a rather severe look from under his blue pointed hat. "What do you mean? Do you wish me a good morning or mean that it is a good morning, or mean that it is a good morning whether I want it or not; or that you feel good this morning; or that it is a morning to be good on?"

"All of them at once." answered Bilbo. Sly, meanwhile, watched the exchange with quiet interest. This fellow was much taller than Bilbo, actually a few inches taller than his own six feet, so was he still a hobbit? His musings were interrupted by Bilbo blowing a smoke ring which, unintentionally, blew into his face, causing him to splutter. At this, the man chuckled, "Why Mr. Cooper, the Old Toby from Mr. Baggins pipe does not seem to agree with you."

"Wait, how do you know-" Sly began, only to be cut off by Bilbo "I don't think I know your name my dear sir."

"I do know your name Mr. Bilbo Baggins and Mr. Sylvester Cooper, though Mr. Baggins, you do not remember that I belong to it. I am Gandalf, and Gandalf means me!" He then proceeded to grumble about "good-morninged" as if he were a passing salesman. But Bilbo paid no attention to this, "Gandalf! Not the wandering wizard! Not the fellow who told such wonderful tales about dragons and goblins and giants? Not the man who made such wonderful fireworks? I beg your pardon but I had no idea you were still in business."

"Where else should I be?" Asked Gandalf. Sly began to feel a bit more hopeful. A wizard? Didn't they have magic? Maybe he could send him home or at least provide some more answers about where he was and how he got there. And then the wizard went on, "I have come to share an adventure with you both. Very amusing for me, very good for you- and profitable too-very likely."

Before Sly could press him, the hobbit squeaked. "Sorry! I don't want any adventures, thank you. Not today. Good morning! But please come to tea- anytime you like! Why not tomorrow? Come tomorrow! Good bye!" Bilbo then scurried into his house and closed the door. Sly turned back around to see the wizard chuckling and, before he could stop him, walk up to Bilbo's door and scratch a curious sign into it. As he walked off the lawn, Sly called after him, "Wait! How do you know me? What is going on-?" But before he could continue, the wizard stopped and said "I promise you I will give you answers but not now. I have business to attend to. By the way, you may want to tell Bilbo to prepare for 14 guests tomorrow." And without a backward glance, strode off towards the road and vanished into thin air.

AN: I am sorry to all major Tolkein fans for butchering a lot of Gandalf's and Bilbo's quotes from the book. I just didn't think that using the whole quotes worked with this story.

Anyway, I am trying to decide whether I should include the rest of the Cooper gang in the story. Any thoughts?


	2. Chapter 1: Expect the Unexpected

Hello there again! I am so glad to be back!

Sly: Shouldn't you be studying?

Me: What the-?! How the bloody hell did you get here?

Sly: Why are you asking me that? A) I'm a master thief B) It's your work

Me: ok, fine. Anything else, you'd like to add before we start?

Sly: Please don't torture me. (Gives pleading baby eyes)

Me: Not my intent. We'll just have to see where the story takes us J

Sly: Mean

Disclaimer: I do not own anything from the Hobbit/Lord of the Rings or Sly Cooper franchises

Chapter 1: Lesson 1- Expect the Unexpected

Sly stood rooted to the spot. Here was someone who had answers for him and the guy just _vanished_. Granted he could (and often did) do the same but still, it was annoying. Grumbling quietly, he made his way back into the hobbit hole, careful to avoid hitting the chandelier with his head. As he continued to grumble about the wizard he suddenly halted. _Wizard, wizard, WIZARD! Bentley!_ As this thought came to him, he quickly reached down into his leg pouch which he had put back on earlier and brought the binocucom (AN: again not sure if this is spelled correctly) up to his eyes. Static. That's all he got.

Sighing, Sly made his way into the kitchen where Bilbo had begun to bake, presumably to calm himself down. Sly noted that his hands were still trembling. The least he could do was help Bilbo after he had provided care earlier "May I offer some assurance?" Sly asked. Bilbo jumped; he hadn't noticed the thief's entrance, which, he mused, shouldn't have surprised him assuming the stories he had told earlier where true.

"Oh?" Bilbo questioned after he had recovered. "What might that be?"

"This may sound insulting but, as a thief, one of the first rules is to expect the unexpected" Sly said calmly.

"Really" said Bilbo rather shortly, he was still a little shaken up from earlier after all. (Blasted wizards scaring gentle folk like that-).

"Really" replied Sly, interrupting his thoughts "For example, the wizard just mentioned that you are about to have fifteen guests rather than the one you expected." Bilbo stood their gaping at him, trying to find something to say.

"T-Thank you" he stammered. "I shall bear that in mind. B-But fifteen guests! Oh no! I don't have enough food for everyone! And who might these guests be?"

"Not sure, but again, expect the unexpected, especially with this Gandalf fellow."

At that, Bilbo was off, baking up a storm of cakes and running down to the butcher & winery, getting enough food for a small army. Sly chuckled. This would be very interesting. Even better, he would get answers. 

The next evening, Sly and Bilbo were just finishing their supper when a knock came at the door. Bilbo promptly got up and opened the door for their guests while Sly melted into the shadows. For at the door was not the wizard but a man slightly taller than Bilbo. This is where the similarities ended, the guest was very muscular with a short beard, braids on the sides of his bald scalp, with heavy armor on under his cloak and a very stern air. _Is he a hobbit like Bilbo?_ Wondered Sly, _But Bilbo said hobbits don't wear shoes_. "Greetings Master dwarf" Bilbo started, inadvertently answering Sly's question, "The food is that way" while indicating to his kitchen table which had begun to groan with the massive amount of food he had prepared. "Thank you" said the dwarf gruffly, "Dwalin at your service." "Bilbo Baggins at yours" answered Bilbo smoothly, leading the dwarf towards the table and handing him a mug of beer. The doorbell rang again. This time, an older dwarf with a long white beard waited on the doorstep. "Balin at your service." "Good evening" replied Bilbo, taking his cloak. "Am I late?" Balin inquired. "No, I think you might be early." Mused Bilbo as he made his way to the pantry to grab some seed cakes for Balin. While Bilbo was gone, Sly observed as both newcomers greeted each other in a very familiar manner. Judging by the greeting and their names, they seemed to be brothers. Just as Bilbo entered the room, both dwarves grasped each other's shoulders and head-butted each other, making Sly wince from his hiding spot.

 _When is Gandalf going to get here?_ Thought Sly impatiently. He was getting rather restless as it was rather cramped due to him trying to hide in a rather small hobbit hole but didn't want to reveal himself yet, not sure of these new strangers. For the third time, the doorbell rang, this time revealing a pair of younger dwarves, one with blonde hair while the other sported raven locks. "You must be Mr. Boggins!" exclaimed the dark-haired dwarf. Sly snorted, unable to help himself. Balin's eyes whipped around but he couldn't spot Sly as he blended into the background. After a long pause, he shrugged and drank some more beer. Meanwhile, Bilbo had rather stiffly answered, "It's Baggins and the others are this way." The blonde dwarf clapped his hand onto his companion's shoulder and said "Thank you, Mr. Boggins, we were worried it might have been canceled" with a wicked twinkle in his eye. "Fili- and Kili" interjected the dark-haired dwarf "at your service." Dropping their weapons on the bench by the door, they made their way to Balin and Dwalin and helped bring out more food from the pantry. _I think I might like these two,_ thought Sly, amused with the mischievous pair.

The bell rang for the fourth time. _That is starting to get annoying_. Bilbo seemed to be getting annoyed too. He grumbled about dwarves and wizards and having to expect the unexpected all the way to the door. When he opened it, seven dwarfs tumbled face down onto his welcome mat. Behind them, still outside the door, a tall figure bent down and peered inside. "Gandalf" sighed Bilbo.

Sly continued to observe the dwarves as they bustled about. The seven who had arrived seemed to be named Oin (an older dwarf with an ear trumpet), Gloin (he had a long red beard), Dori, Nori, Ori (who seemed to be rather young), Bofur, Bombur (who was very fat) and Bifur. Bifur and Bofur easily stood out the most as Bofur had a large hat on while Bifur _had a freaking axe stuck in his forehead_. How the dwarf was still alive, Sly did not know. "Well, well Mr. Cooper. I see you have yet to join the party" observed a familiar voice jovially. All the dwarves stopped what they were doing and looked over towards Gandalf. Heaving a sigh, Sly stepped forward into the light.

The reaction was spectacular. Everyone, minus Bilbo and Gandalf, yelled out. Some grabbed their weapons, Dori shoved Ori behind him, and others, like Balin just stared. "I suppose I should introduce myself." Sly drawled lazily, having secretly gotten a kick out of the uproar. "Sly Cooper at your service." Slowly, the tension bled out of the room and was replaced with curiosity. Surprisingly, it was the seemingly timid youngster Ori who stepped forward and asked, "May I ask _what_ you are, if it isn't too rude" he added timidly. Dori shoved Ori behind him again and glared at Sly protectively. "I am many things" answered Sly wickedly, enjoying this. "A master thief for starters." Now everyone gaped at Sly. Using his cane, he snagged a doily from Bofur. "I don't think Mr. Baggins wants his crochet ruined." Sly mentioned smoothly. Bofur, having recovered from his shock, quipped back "Oh and what a fine game it is, when you have the balls for it." Sly snickered and offered the doily to Bilbo who hastily put it away.

Grumbling, the dwarves put away their weapons. Sly decided that this was a good time to ask the wizard his questions, since he had revealed his hiding spot. However, he was intercepted by Fili and Kili. "Mr. Copper" started Kili. "It is a pleasure meeting you this fine evening" finished Fili as they both smirked. Though he was a little annoyed about not being able to speak with Gandalf immediately, he couldn't help but smirk back at the two. "A pleasure indeed. Tell me you were Felipe and Kelly right?" he purred. The two stared at him then broke into raucous laughter. "I think his fur grew between his ears, eh Fili?" "I agree brother" snickered Fili. "Well my fuzzy friend, I think we shall get along fine." "Oh, I should hope so" put in Sly, "and by the way, were you missing these?" and held up two sacks of coins. Both brothers hurriedly felt their pockets only to find them empty. "I shall take that as a yes." Sly's smirk grew larger as he handed the money back to the stunned brothers. "He's good. The fuzzy man is good." Kili snickered.

At that moment, Ori walked up to a rather flustered Bilbo and politely asked him where he should put his plate. "Here you go Ori, give it to me." Called Fili. To Bilbo's immense displeasure and Sly's amusement, Ori tossed the plate to Fili over Gandalf's head. At the same time, the other dwarves began to use their feet and the cutlery to start a merry beat.

 _Blunt the knives, bend the forks_

 _Smash the bottles and burn the corks_

 _Chip the glasses and crack the plates_

 _That's what Bilbo Baggins hates!_

Sly watched with some amazement as the plates and mugs went soaring across the room, none of them smashing into the wall. Instead they were all caught by Kili who had made his way to the kitchen sink.

 _Cut the cloth, tread on the fat_

 _Leave the bones on the bedroom mat_

 _Pour the milk on the pantry floor_

 _Splash the wine on every door_

 _Dump the crocks in a boiling bowl_

 _Pound them up with a thumping pole_

 _When you're finished if they are whole_

 _Send them down the hall to roll!_

 _That's what Bilbo Baggins hates!_

Having finally made his way to the table, Bilbo was relieved to find they had done none of these awful things and saw that all his plates were clean and neatly stacked on the table.

At that moment, three firm knocks were heard from the front door. "He is here" Gandalf intoned solemnly.

AN: I'm still not sure if I should bring the rest of the Cooper gang in. Please review and let me know what you think.


	3. Chapter 2

**Hi everyone! I hope you have had a lovely weekend. Here is the next part of the story!**

 **Disclaimer: I do not own anything from the Sly Cooper series or The Hobbit/Lord of the Rings universe. These belong to Sanzaru/Sony and JRR Tolkein (and Peter Jackson for some of the movie ideas) respectively.**

* * *

Chapter 2: Lesson 2- Never Sell Yourself Short

"He is here." Amazing how three little words can change the atmosphere in a heartbeat, Sly mused to himself. Gandalf made his way back to Bilbo's front door and opened it. There, on the doorstep was yet another dwarf. However, this dwarf was different than the rest. He had an air of quiet strength and self-importance that probably made others around him stop what they were doing to observe him. The term self-importance may have been a slight understatement from Sly's view, it may have been more appropriate to call this dwarf slightly arrogant.

"Gandalf" stated the new dwarf. "I thought you said this place would be easy to find. I lost my way, twice. I would not have found it at all if not for the mark on the door." Bilbo, having been shown the mark earlier by Sly, merely scowled in silence.

Gandalf noticed his frown and chose to ignore it. "Bilbo, this is the leader of our company, Thorin Oakenshield."

Thorin took a step towards Bilbo with a slight sneer. "So, this is the hobbit." Ok, make that _very_ arrogant. "Tell me, Mr. Baggins, have you done much fighting?" Sly was _so_ going to enjoy messing with this guy when he got the opportunity. "Axe or sword? What's your weapon for fighting?" asked Thorin, circling Bilbo like a wolf around a wounded deer.

"I have some skill at conkers" said Bilbo stiffly, looking Thorin in the eye "But I fail to see how that is relevant." Sly groaned internally at Bilbo's statement though he couldn't help but admire Bilbo's backbone in the face of such scrutiny.

Thorin snorted, "I thought as much." Glancing at some of the other dwarves, he snickered, "He looks more like a grocer than a burglar." Many of the dwarves chuckled at the jab at Bilbo.

A smooth voice broke in, "The _grocer_ is kindly hosting you in his home though you were not invited. I am almost tempted to say beggars can't be choosers because you look more like a beggar than a warrior."

With a snarl, Thorin whirled around to see Sly calmly leaning against the door frame. Thorin spluttered, "Who and what might _you_ be? Some vermin that the stinking elvish folk have sent?"

Unperturbed, Sly made a show of polishing the head of his cane. Here was his opportunity to take this guy down a peg or two and boy was he going to make the most of it.

"My name is Sly. Sly Cooper. As to what I am, I am a thief, a friend of Bilbo's and apparently much more talented at showing gratitude as well as manners." He purred, having guessed at just the right buttons to push. Thorin's face turned the color of bricks. "And just what is _your_ weapon of choice, vermin?" In response, Sly twirled his cane in front of Thorin. Snarling, Thorin tried to use the flat of his sword to stop Sly's blade only to find himself lying flat on his back, staring up at the raccoon smirking down at him, locking ice blue eyes with chocolate ones. "And by the way, you might want to keep a better hold of your money bag" said Sly, jingling the little bag in front of the prostrate dwarf.

"That is enough!" boomed a voice from behind them. Both Sly and Thorin turned around to see Gandalf glowering at them. Muttering about spoilsports, Sly helped Thorin up, who was wary enough of the wizard not to refuse it, and gave him back his money. Thorin swiped the little bag from Sly and made his way over to Balin and Dwalin, making a point to ignore Sly from then on.

Glancing out of the corner of his eye, he saw Fili and Kili silently guffawing and cocked an eyebrow at them. In answer, Fili managed to choke out, "You managed to get under Uncle's skin in less than two minutes. Dammit, you beat our record. I reiterate, you are good."

Bilbo came over. "Thank you for that" uttered Bilbo gratefully. "Think nothing of it. Just remember the second rule of thieves- never sell yourself short." Smiling kindly at Bilbo, Sly made his way over to a less crowded corner and sat. He didn't like how Thorin belittled Bilbo, it reminded him too much of how Bentley was bullied when they were kids. In fact, Bilbo was a lot like the turtle. Though he wasn't a technological genius, Sly could see that Bilbo had more to him than met the eye as evidenced by the quiet bravery he showed while enduring Thorin's scrutiny.

His musings were cut short when he noticed that the dwarves had formed a sort of council at Bilbo's dining table once Thorin had finished eating. "What news from Ered Luin?" asked Balin. Dwalin quietly added, "Are the dwarves of the Iron Hills with us?" Somberly, Thorin answered, "They will not come. This quest is ours alone." After the dwarves finished groaning, Gandalf laid a map out onto the table.

* * *

"Far to the east, beyond wastes and woodlands, lies a single solitary peak."

"The Lonely Mountain" murmured Bilbo. "Oin has read the portents" began the red-bearded Gloin (AN: I think it's Gloin) "and the portents say it is time. Ravens have been seen flying back to the mountain." As the other dwarves muttered their agreement, Sly noticed Gandalf lighting his pipe with a flame that seemed to be produced from his fingers. Gandalf winked at him.

"The reign of the Beast shall end." Finished Oin (AN: I think). Both Sly and Bilbo perked at the word "beast". "And this beast is…?" asked Sly delicately. "Oh, that would be a reference to Smaug the terrible, chieftest and greatest of calamities." Answered Bofur. "Airborne firebreather. Teeth like razors, claws like meat hooks. Extremely fond of precious metals."

Bilbo cut in, "Yes, I know what a dragon is, thanks." _A dragon?_ Wondered Sly, a horrible suspicion starting to settle in. _What's a dragon got to do with Bilbo?_

Ori suddenly stood up. "I'm not afraid. I'll shove some dwarvish iron right up his jacksie!" He declared before being pulled back down by Dori. "Ah but you forget, we'll need an army at our backs. And we number just thirteen" observed Balin. "Nor thirteen of the best nor the brightest."

Fili protested, "We may be few in number, but we are all fighters, every last one of us." Kili chimed in, "And you forget we have a wizard in our company, he'll have killed hundreds of dragons in his time." Hearing spluttering, Sly looked to the wizard who began to mutter "Well now, I wouldn't-." But Dori cut in, "Well, how many have you killed?" When Gandalf began to indignantly cough around his pipe, Dori persisted "Well, go on, give us a number!" And the table erupted into argument. Sly privately felt that this was a fair point for the dwarves.

A sudden shout from Thorin had the dwarves back in their seats and quiet. "If we have read these portents, do you not think that others will have read them too?" He began. "Smaug has not been seen for 60 years. Eyes look east to the mountain, assessing. wondering. Does the vast wealth of our people now sit unprotected? Do we sit back and let others take back what is rightfully ours?" And with that the dwarves began to chant what sounded to Sly like "Du Bekar."

Then Balin, who seemed to be a bit of a Debbie Downer, asserted, "You forget the front gate is sealed. There is no way into the mountain."

"That my dear Balin is not entirely true" answered Gandalf, leaning forward and producing a metal key.

Staring at it, Thorin asked, "How came you by this?" And Gandalf replied, "It was given to me by your father, Thrain, for safe-keeping. It is yours now." Thorin took the key with a look of reverence, one that Sly, despite not liking the dwarf could relate to. It was the same look he himself wore when he had first looked upon the completed Thievius Raccoonus after defeating the Fiendish Five.

"Then there is a door." Fili stated with hope in his eyes. "A secret side door." _Yep, a door that leads to a friggin' dragon!_ Thought Sly. "It may have been secret once, but how do we know that it is secret any longer? Old Smaug has lived there long enough to know about this and all doors."

"He may, but he can't have used it for years" answered Gandalf. "It is too small. 'Five feet high the door and three may walk abreast' say the runes" Gandalf elaborated, indicating the map.

Bilbo, who had gotten excited despite himself, squeaked, "It seems a great big hole to me!" "Yes, my dear Bilbo, and that is where you and Mr. Cooper come in" said Gandalf with a twinkle in his eye.

 **AN: I am going to end it here for now because it is getting too long, even with me changing some of the quotes (from both the book and movie) to speed things up a little. I will try to keep the lengths of my chapters consistent. Please let me know if I have mixed up any of the dwarves**

 **Sly: good for you, I'm getting bored.**

 **Me while grinning evilly: enjoy being bored, it will not last**

 **Sly, smirking: Well at least I can keep the dwarves straight**

 **Me: GODDAMNIT STOP REMINDING ME**


	4. Chapter 2 Part 2

**Disclaimer: I do not own anything from the Sly Cooper universe or from Middle Earth- the books or the movie. They belong to their respectful owners.**

Chapter 2 Part 2- Never Sell Yourself Short

Sly, who had been in the process of standing to take a closer look at the map stilled at the mention of his name. The dwarves also, caught up in their planning, had forgotten about the strange raccoon and stared at both him and Bilbo.

"Me!" squeaked Bilbo. "Yes, indeed" stated Gandalf. "I tried to find a Warrior or a Hero, but they are busy fighting each other in distant lands and in this neighborhood, heroes are scarce. That is why I settled on _burglary_ especially when I remembered the existence of a side-door. And here are Mr. Baggins and Mr. Cooper, the chosen and selected burglars. So now let's get on and make some plans."

"Very well then, supposing the burglar-expert and our furry friend give us some ideas or suggestions" said Thorin mockingly. Ignoring Bilbo, who was spluttering at being called an expert burglar, Sly answered. "It would be a lot easier to give you suggestions if we had a clearer idea of what is going on. For a start, what's the story behind this dragon, Smog, and your homeland."

"It's _Smaug_ , for starters. And haven't you heard of him before?" asked Thorin incredulously. When the raccoon merely shrugged, the dwarf gave a sigh. "Oh, very well. Long ago in my grandfather Thror's time, our family was driven out of the north down to the Mountain which was discovered by my ancestor Thrain the Old. Thror was named King under the mountain and our family grew immensely rich from mining gold and precious jewels." At this point, Thorin began to wax poetic,

"For ancient kind and elvish lord

There many a gleaming golden hoard

They shaped and wrought and light they caught

To hide in gems on hilt of sword"

At this point, Sly hastily interrupted "so your family ruled this mountain. Where does the dragon come in?" Thorin sniffed, "Do not interrupt. Anyway, what brought the dragon was undoubtedly the wealth of the mountain. Dragons steal gold and jewels, you know, and they guard their plunder as long as they live (which is practically forever, unless they are killed) and never enjoy a brass ring of it. One day, this worm Smaug flew up into the air and came south. The first we heard of it was a noise like a hurricane. I was on the ramparts at Erebor and saw the dragon land on our mountain, shooting fire in every direction and crushing mine people beneath his foul claws."

Thorin stopped for a moment to regain his composure. "He had just destroyed the great town of Dale where men lived beneath the splendor of our home. The worm came through the front gate of Erebor and stormed into the treasure room, but not before killing hundreds of dwarves and men. I survived and lead the remainder of our people to safety. For years, we have wandered the lands, trying to make a home and living for ourselves. But we have never forgotten our homeland. And now is the time to reclaim it!"

Sly winced. Again, he found that he could sympathize with Thorin as he himself had lost his home when he was eight years old, also at the hands of a monster. _And thank goodness that there are no dragons where I'm from. Kaine Island would have been a prime target. Dr. M was hard enough to defeat, forget about fighting a dragon_.

Bilbo, having been momentarily forgotten piped up, "Well, it sounds like you need a very good burglar."

Everyone looked at him. "And are you?" inquired Balin. "Am I what?" responded Bilbo, confused. "He said he's an expert!" Oin exclaimed happily. "Oh no, no, no, I'm not a burglar, I've never stolen a thing in my life." Bilbo strongly negated. "I'd have to agree with Mr. Baggins" said Balin solemnly. "Aye, the wild is no place for gentle folk who can neither fight nor defend themselves" added Dwalin.

At this, Gandalf abruptly stood. Sly made a careful retreat as the shadows loomed over Gandalf, making him seem twice as tall than he normally stood. "ENOUGH! IF I SAY THAT BILBO BAGGINS IS A BURGLAR THEN A BURGLAR HE IS!" Though he remained standing, the shadows retreated. "Hobbits, as well as Coopers, are remarkably light on their feet and can pass easily unseen. You asked me to choose the fourteenth member of this company and here he stands along with the fifteenth member."

With a grunt, Thorin nodded. "Balin, give him a contract. Figure something out for _the raccoon_." He finished disdainfully. Ignoring Bilbo's protests, Balin handed him a large packet of parchment. "This is just a document covering the basics- travel arrangement, out-of-pocket expenses, funeral arrangements-".

"Funeral arrangements! And what's this about evisceration and incineration?" exclaimed Bilbo reading from the contract. "Oh aye, he'll melt the flesh off your bones in the blink of an eye" Bofur responded cheerfully. "Just think giant furnace! Searing pain one moment then poof! You're nothing more than a pile of ash."

They watched as Bilbo pondered this for a moment. "Um, nope" muttered Bilbo and he dropped in a dead faint.

Bilbo dimly made out a cheerful fire and a fuzzy figure, who, despite his returning eyesight, remained fuzzy. He sat upright with a start, finding himself in his favorite armchair in his sitting room. In the room with him was Sly, who was giving him a concerned look. "Are you alright?" he asked. "I'll be alright, let me just sit quietly for a moment."

"You've been sitting quietly for far too long" snapped a voice. Gandalf strode in, giving Bilbo a disapproving look. "When did your mother's doilies and dishes become so important? I remember a young hobbit who longed to find out what was beyond the borders of the Shire. The world is not in your books, it's out there."

"I can't just go running off into the blue. I am a Baggins of Bag End!"

"You are also a Took" retorted Gandalf. "Did you know that your great-great-great uncle Bullroarer Took was so large he could ride a horse? Well, he did, and when he charged the goblins he swung his club so hard that it knocked the goblin king's head clean off and down a rabbit hole. Thus, he won the battle and invented the game of golf at the same time."

"I believe you made that up" muttered Bilbo, Sly privately agreeing. "Well, you'll have a tale or two to tell when you come back" Gandalf observed. "Can you promise me that I will come back?"

"No, and if you do you will never be the same." Shaking his head, Bilbo stood. "That's what I thought. I'm sorry Gandalf I cannot sign this." With that, he exited the room, leaving Sly and Gandalf staring after him. As Gandalf smoked his pipe despondently, Sly remarked, "I still think he shouldn't sell himself short like that."

"I know this isn't a good time but earlier, you said that you had answers for me. What did you mean by that? Do you know how I got here and how I can get back home?" asked Sly expectantly. The wizard sighed and looked up at the thief. "I have some idea of both how you got here and how to get you home, but Thorin will need to be in here for the latter answer. Let me answer the former then. I believe that your arrival was no mere coincidence but was set by the Valar."

"Who?" asked Sly. "You would call them angels in your world, and they answer to the creator Eru Iluvatar (AN: I am not a Middle Earth expert and may be spelling things wrong as well as messing some facts up). However, they are very similar to the Greek deities of your homeland. It is my belief that when you were thrown through time, they took this as an opportunity to enlist your help, however unwillingly."

Here Gandalf chuckled slightly, "After all, it's not like you cannot get home again. For you are not the first Cooper to set foot in Middle Earth."

 **EVIL CLIFFHANGER! Who could this mysterious Cooper be? If you want, you can type some reviews down (at this point I am BEGGING for a review). Otherwise, you'll just have to wait and see who I come up with.**

 **Sly: uh, who gave you the right to mess with my family tree? Especially since I have JUST BEEN THROWN THROUGH TIME TRYING TO SAVE THEM.**

 **Me: The fanfiction deities. Muwahaha**


	5. Chapter 3

**I'm back! Well, it's only been a week but still. Anyway, onto the next installment!**

 **Disclaimer: I do not own anything from the Sly Cooper universe or from Middle Earth.**

Chapter 3: Always strike a good deal

Sly gaped at the wizard. "W-What!" He stammered. "Yes, indeed" replied Gandalf with a twinkle in his eye. "B-B-But who? How? When?"

"Your ancestor, one Slytunkhamen, stumbled into Middle Earth many years ago. In fact, he came just before Smaug brought ruin to the mountain kingdom of Erebor. How he came to be here, I know not, but I do happen to know how he managed to get back."

"You do? How?" questioned Sly, hope rising within him. "I shall inform you of that once Thorin arrives."

"Can you at least tell me why I am here then? What do these Valar want from me? I'm just a thief" Sly argued. Gandalf regarded the raccoon thoughtfully for a few moments. "I am not entirely sure myself, but I should think that, as a thief, you will be most helpful to helping the dwarves reclaim their homeland. And to Bilbo. Perhaps that is why the Valar brought you here. What I can tell you for certain is that the reason will become clear with time. Ah, here is Thorin."

Thorin, indeed, had just strolled into the room. "Well" he sniffed "it seems we have lost our hobbit burglar. What of the raccoon?" Sly fought the urge to sneer at Thorin's way of speaking about him as if he wasn't standing right there.

"Mr. Cooper shall be accompanying you on your quest." At both of their questioning looks, Gandalf elaborated. "For that is how young Sly shall return home." His attention fixed entirely on the grey wizard, Thorin insisted "Explain."

Gandalf ignored his tone and began "I believe Thorin you will remember white gems of pure starlight on a chain of white gold." The dwarf sneered, "Yes, the wedding gift of the elf scum. What of it?"

"Those gems are indeed made from starlight and, with the right words, be used to form a portal between our world and Mr. Cooper's." Sly stared at him. "You mean there is a way back? I can go home?" breathed Sly, daring to hope. "Yes, there is. But I must warn you that the journey is long and hard. I believe that, in exchange for your services, I think it would be quite fair to let Mr. Cooper borrow the gems for his journey home, eh Thorin?" The wizard inquired of the dwarf who did not look pleased.

"Fine. If Mr. Cooper upholds his end of the bargain, he may have the gems." Said Thorin after a lengthy silence. "Wait" interjected Sly. "What exactly is my end of the deal? What am I supposed to be stealing?"

After a suspicious look, Thorin relented. "The Arkenstone."

"The what?"

The dwarf king sighed. "The Arkenstone. A large white gem that you will know immediately upon sight. It is the symbol of my people and my right to rule. Return it to us and when we retake the mountain, the elf gems are yours to do with as you see fit."

Sly regarded him. He did not like the arrogant dwarf, but he sensed no dishonesty or treachery in his words. Besides, it was currently his only way back. "Then it's a deal."

* * *

Thorin left the room to inform Balin of the tidings (and of what to specifically put in Sly's contract). Sly himself wandered into the kitchen to where the other dwarves lingered. To his surprise, the bald dwarf ( _Dwalin, I think_ thought Sly) marched up to him.

Sly merely asked "May I help you?" To which Dwalin merely growled. "I'm watching you." He finally grunted and walked off. Balin, who had quietly been watching, chuckled. "Well laddie" he said when he noticed Sly's questioning look. "This will be an interesting journey."

Rolling his eyes, Sly shook his head and went to bed. (AN: Rhyme!)

* * *

The next morning, Sly felt a sharp rap on the shoulder. "OW!" He yelped. Kili and Fili grinned back, having whacked him. "Rise and shine my fuzzy friend!" Kili positively leaked rainbows and sunshine, making Sly sweat-drop. "But it's so early" Sly whined, groggily. Raccoons were mostly nocturnal after all and Sly was no exception, especially considering his career. Fili snorted, "Early or not, Uncle wants to get going. He's not sticking around to see if Mr. Boggins will have a change of heart. So, get up." With that, the twins left for the kitchen.

Grumbling about how non-nocturnal folk simply couldn't understand, he got up and gathered his gear. He gave a longing look at his binocucom, which still showed static, then made his way to the kitchen as well for a quick breakfast.

An hour later, he stood outside an inn named the Green Dragon with the other dwarves. He wondered whether Bilbo would find the note and found himself hoping that the little fellow would change his mind. Partially because he liked the little fellow. Also, because he had bet ten gold coins with Kili and Fili that he didn't have (AN: I don't know the currency in Middle Earth).

As he surreptitiously surveyed the hobbits bustling around, Dwalin stomped up to him. "There's your ride" he grunted, indicating a gray gelding placidly nibbling at the grass. Sly stared at him. He really should have expected this. And he actually did know how to ride, courtesy of his stay during Sir Galleth's time. The knight had thought it ludicrous at first that they required a machine for travel and insisted that any descendent of his should at least know the basics of riding a horse. So, after a small gulp, he nodded.

The twins came over just as he hauled himself into the saddle. "Don't you find it odd?" Kili questioned innocently. Sly steeled himself for what he knew was coming. "I mean" continued Fili "You're both furry, have a tail and are gray." Sly just smirked back. "Don't you find it odd" started Sly "how you have to finish each other's sentences?" The twins looked at each other.

"No" they stated simultaneously. "Well, there's your answer." And he left them to ponder that.

"Forward" Thorin called out. Sly rode the gray horse, who he decided to call Shadow, behind Gandalf and in front of Dwalin. Trying not to focus on the warrior's eyes drilling a hole in his back, he attempted to move Shadow forward enough to get a word with Gandalf. He wanted to learn more about what Slytunkhamen was doing so far from Egypt. But before he could, he heard shouting.

"Wait, wait!" Sly turned around on Shadow. There, running up behind the company, was Bilbo, clutching the contract. As the company halted, Bilbo caught up. Beaming at them, he declared "I signed it." He handed the contract to Balin, who gave a mock-stern look at Bilbo before inspecting the signature. "All seems to be in order" Balin announced. "Welcome Mr. Baggins to the Company of Thorin Oakenshield."

Thorin grunted. "Get him a pony." Ignoring Bilbo's protests, Fili and Kili rode up behind the hobbit, grabbed him by the arms and deposited him onto the back of the spare pony. As Bilbo settled in, the hobbit jolted. "No, wait, wait, stop! We have to turn around." Gandalf came over, "What on earth is the matter.?" "I forgot my handkerchief."

Sly couldn't help it. He burst out laughing as Bofur ripped a piece of cloth for him to use. By the time he managed to calm himself down, the Company had started moving again. Small bags suddenly flew through the air, one of them landing in his lap. Upon opening it, he found ten gold coins and sent a smirk towards Fili and Kili who looked sulky. "What are they doing?" Asked Bilbo. Sly filled him in, "They took bets on whether you would come."

The hobbit harrumphed. "Well, I see you thought so. But what about you Gandalf?" At that moment, a bag landed in Gandalf's lap. "My dear fellow, I never doubted you for a moment."

"How did you know I would change my mind?" Bilbo asked Sly. "Simple. Rule 3 of being a thief is to always strike a good deal."

"And how precisely is this a good deal for me?" Bilbo asked irritably. "Because you actually get to see the world and help people at the same time. Not to mention get relatively rich, from the way these dwarves have been talking."

 **And they have left the Shire!**

 **Sly: Finally**

 **Me: Yes, things have been a little slow but now the adventure begins. Besides you should be grateful that you know how to ride a horse (courtesy of me).**

 **Sly: really**

 **Me: Yes really, those lessons (and the pants that I have neglected to tell our audience that you are wearing) will help prevent you from getting sores in uncomfortable places. To the audience, have a wonderful weekend!**


	6. Chapter 4

**Hello everyone! I am back after having a busy few weeks!**

 **Disclaimer: I do not own Sly Cooper or The Hobbit. I have used quite a few quotes from both the movie and the book and these belong to their respectful owners. Please read and review (seriously I might keel over dead from joy if I ever actually manage to get a review on this).**

Chapter 4- Gather information

The trip didn't seem too bad at first. They passed through the rest of the hobbit lands which seemed to be a wide respectable country, much like the Shire. Next, they rode into lands that seemed to be somewhat forsaken, with no inns and where the roads grew steadily worse. On the second day of passing through these "Lone-lands" as Gandalf called them, they made camp at the base of a dreary hill, under an overhang trying to take shelter from the rain. Sly noticed at the top of this hill seemed to be an old castle that, from the look of things, seemed to be abandoned. So while the others sat around the fire, Sly, along with a reluctant Bilbo, went exploring. Sly had insisted the little hobbit come with him for "thief training".

"To think it will soon be June!" grumbled Bilbo as splashed along beside Sly up the hill through the pouring rain. The raccoon ignored him, too intent on the castle. His Cooper instincts were tingling, and whenever they did so, Sly paid close attention. At the castle entrance, he stopped and turned to Bilbo who was still grumbling.

"Now it is time" began Sly "to begin your instruction in the ancient and noble-" Here Bilbo snorted, causing Sly to glare at him until he had hastily disguised it as a sneeze. " _Noble_ art of thievery. The first thing to do when you have reached your target's home is to find the best point of entrance as well as escape routes for when you are done." Looking around, Sly saw that the best entrance point was, for once (minus one particular time in feudal Japan), the front entrance.

"Alright…" trailed Bilbo "so, we've found the entrance, what next?"

"Now, we enter, quietly and remember, absolutely no sound. Watch and listen." So saying, Sly seemed to melt into the shadows of the old castle, moving silently across the dusty floor, his feet making no sound against the ancient stone. When Sly had moved a fair distance into the castle, he motioned for Bilbo to join him. He watched as Bilbo quietly made his way in.

"You may not have looked very sneaky" Sly said when Bilbo reached him, "but you are surprisingly quiet."

"Thank you" sniffed Bilbo. "Now what?"

"Now we find our objective."

"And that is?" enquired Bilbo. "You'll know it when you see it." Sly answered, for he himself was not entirely sure what he was looking for. He and Bilbo were standing in the remnants of a front hall, at the base of a great, stone staircase. The unlikely duo climbed the stairs and quietly wandered through the halls, Bilbo following Sly's lead in sticking to the shadows. While he would never admit it, Bilbo was secretly beginning to be excited by this thief business. Suddenly, they found themselves in what looked to be an ancient library, filled with several massive tables which were surrounded by shelves filled with dusty, moth-eaten tomes.

A gleam from one of the tables caught Sly's attention. Walking over, he blew dust off of a small box. Then he gasped. "What?" asked Bilbo. Peering around Sly's elbow, he saw the box had a small etching of what looked like- "Is that your cane?"

Silently, the master thief nodded. He opened the box. Inside he found some papers, which he scooped up, leading him to gasp again. For underneath the papers was an eye. A very familiar eye. A Clockwerk eye.

 _How is this possible?_ Thought Sly. _He was back in my world when I killed him. Twice. And destroyed all his body parts with the hate chip!_

Thinking quickly, Sly grabbed the eye as well and slid it into his backpack. He was determined to get answers about his ancestors at the first opportunity. "What are those?" Bilbo asked gingerly, for he sensed the turmoil Sly seemed to be going through. Shaking himself out of his mood, Sly grinned down at Bilbo. "Just a bit of family history. Speaking of which, I want to teach you a technique developed from one of my first ancestors, Slytunkahmen II. The shadow walk." So saying, Sly instructed the hobbit on how to turn himself invisible. Try as he might, Bilbo simply could not do it. "Don't worry" Sly reassured him "it takes a lot of practice. I want you to try that whenever we stop at night. If you can sneak up on any of the dwarves or, even better, Gandalf, you'll be more than ready to face a dragon. If it helps, just stand still and touch your top button." Curiously, Bilbo tapped the top button of his coat and asked why. Sly just shrugged and answered, "I always remember to jump and hit the circle button." Which just confused Bilbo even more.

They left the castle, Bilbo with more knowledge and Sly with more questions. Once they reached camp however, they found that most of the dwarves were already on their ponies waiting for them. After berating them for sneaking off, Thorin demanded that everyone move out immediately, preventing Sly from confronting the wizard _again_.

 _At this rate, I'll never get answers_ Sly grumbled to himself. At least he had some papers to look at, though he resolved not to do so while out in the wilderness to prevent ruining them. He also decided that it may be a good idea to wait to confront the wizard when they weren't constantly on the move. He sighed. "Why is it so hard to get answers so hard" he whined to Shadow, who nickered as if he was laughing. Sly sniffed, "Well, I'm glad someone enjoys my misery" he grumbled.

* * *

That night, they made camp along a cliff as the weather had cleared up. Bilbo was in the middle of sneaking an apple to his pony Myrtle when suddenly, a howl tore through the night. Sly sat upright from his position of leaning back against an old oak tree. "What was that?" asked Bilbo. "Orcs" answered Kili. "Orcs?!"

Sly could see Thorin, Balin and Gandalf were all awake while everyone else was asleep. Everyone except Fili and Kili. And they were clearly having fun scaring the hobbit. "Throat-cutters" Fili continued. "There'll be dozens of them out there. The lowlands are crawling with them." At Bilbo's worried look, the twins began to snicker.

"You think that's funny?" Thorin loomed behind Bilbo, glaring at his nephews. "You think a night raid by Orcs is a joke?"

Shame-faced, the brothers looked away. "We didn't mean anything by it." Kili mumbled.

"No, you didn't. You know nothing of the world." With that, Thorin went to brood at the cliff edge. While Sly wasn't as amused at the twins teasing Bilbo, he felt that Thorin's reaction was a little harsh.

"Don't mind him laddie." Balin came over to Bilbo and the twins with a sympathetic look. "He has more cause than most to hate Orcs."

Balin launched into the tale of how a young Thorin fought in the battle to win back another homeland called Moria and how he had to watch his grandfather get killed by a white orc named Azog. Sly shifted uncomfortably, reminded of how he himself had watched his father's murder by a group of monsters called the Fiendish Five. After hearing Balin recount Thorin's battle against the white monster, Bilbo asked "And the Pale orc? What happened to him?"

"He slunk back to the hole from whence he came" Thorin snarled from the cliff. "That filth died of his wounds long ago." Sly did not miss the look exchanged between Gandalf and Balin. Had the pale orc survived? Why didn't Thorin finish the deed then and there on the battle field? Sly had learned the hard way that some opponents needed to be dealt with immediately after the Klaww gang fiasco. He lowered his hat over his eyes and tried to get some more sleep. How he missed being able to discuss things with Bentley!

 **Hello everyone! Sorry I wasn't able to update this for a while. My life has gotten busy lately. Unfortunately, this means that I may not be able to update anything for a few weeks but I shall be back by the latest May!**

 **Sly: Good grief! I'll be old and dying by the time we have any real action.**

 **Me: I know, don't blame me, blame my exams and work experience! But don't worry, you'll get to meet trolls next time!**

 **Sly: Wait, what?**

 **Me: Evil laugh**


	7. Chapter 5

**Sly: (Gasps mockingly) I thought you were dead! And that you had left me to suffer with very annoying people!**

 **Me: Oh shut up, life happens. Besides, I don't expect you to complain about boredom after this chapter.**

 **Bilbo: But frankly speaking, miss, you have left the readers hanging.**

 **Me: I know (cries quietly in a corner) but I shall try to make it up to them!**

 **Disclaimer: I do not own any characters from the Sly Cooper series or from the Hobbit. In this chapter, I may have given one a name however, read to find out!**

Chapter 5: Play to your strengths

The following morning was horribly wet and horribly dreary. Sly had never been a fan of water to begin with and the discoveries and unsolved mysteries combined with the weather put him in as horrible a mood as everyone else. Thorin's relentless pace was also getting on his nerves. He wanted answers and he was going to get them!

His internal grumblings were interrupted by Gloin. "Here, Mr. Gandalf, can't you do something about this deluge?" The wizard, looking none too happy, merely huffed and replied, "It is raining, master Dwarf, and it will continue to rain until the rain is done! If you wish to change the weather of the world, you should find yourself another wizard."

"Are there any? Other wizards?" asked Bilbo. Gandalf then proceeded to describe the two blue wizards whose names he had conveniently forgotten, the white wizard Saruman and Radagast the brown. This Radagast fellow sounded as if he might get along very well the Aborigines Guru who took Murray under his tutelage, Sly mused, his gloom growing as he was yet again reminded of his family.

"What about you Sly?"

"Hmm?" Sly was broken out of his morose train of thought by Bilbo who was looking at him with curiosity. "What about me?"

"Are there wizards in your world that can change the weather?" Bilbo clarified.

Considering, Sly answered, "Magic isn't common in my world and there is no order of wizards to my knowledge. However, technology can do similar things. Raleigh, a frog pirate, used a flying machine to make the rain around his lair endlessly stormy so ships would sink and leave him free to take their loot."

At the companies heightened interest, Sly continued, "But there have been times that I have had to fight against dark magic and have had magic users help me and my friends in our adventures."

Before he could elaborate about Mz. Ruby and the Guru, Thorin called out "We shall make camp here tonight." As the dwarf dismounted in a clearing with what was clearly an abandoned house, Sly watched slightly miffed. It was as if any time he tried to talk with anyone in the company aside from Bilbo, the annoying dwarf put a stop to it. Shaking his head, he dismounted Shadow and set about helping set up camp.

However, as he stretched his tired limbs, raised voices from the abandoned farm house caught his attention. Silently making his way over, Sly caught the last bits of the argument between the wizard and the dwarf leader.

"I did not give you that map and key for you to hold onto the past!"

"I did not know that they were yours to keep." Thorin answered snidely.

As the wizard stormed off to "seek the only one around here who has any sense" Sly quietly followed after him using his Shadow Walk. He wanted answers and he was going to get them.

After some time, just as Sly began to wonder whether he should say anything, the wizard sighed and turned around to peer at the spot where the raccoon was standing.

"What are you after young Master Cooper?"

"Answers" Sly replied as he revealed himself (not that it was really necessary). "For starters, how did you know me? I know that you said my ancestor Slytunkhamen had come here before, but you knew my name? And for the love of everything pure and holy, why is this here?!" He asked, brandishing the metallic eye while starting to panic. "I killed the monster, twice now, do I have to face him again? Is that the real point of me trying to help Mr. Stick-Up-His-Ass on his journey? How can you expect me to-"

"ENOUGH MR. COOPER!" Gandalf boomed, cutting Sly off mid-rant. As the thief startled, Gandalf's eyes softened. "I understand your concerns and I will answer what I can. It will do no one any good, however, if you simply panic."

They made their way over to several small boulders nearby where they sat, and Gandalf started a fire. Gazing into it, the wanderer started, "As for your first few questions, I knew your name because I overheard you introduce yourself to our estimable Mr. Baggins." Sly gave him a flat look because, nope that's not creepy at all.

"But onto more serious matters. The eye you hold in your hand did indeed belong to an evil owl, though he had not always been so. When he came with your ancestor, he went by the name of Bubophet. The two had, through some magical means that I am not familiar with, managed to create a portal between the two worlds- whether by accident or not, I am unsure. In any case, they ended up in Middle Earth, specifically near Rivendell. From there, they, through many adventures I am sure, made their way to the dwarven kingdom of Erebor where they dwelled for some time before-"

At this point, Gandalf was cut off by the sound of war cries in the distance. With a quick glance at each other, they raced back to the dwarven campsite only to find it empty. Sly mentally cursed himself, how could he have left Bent- no Bilbo- on his own? Finding them was no challenge as a large bonfire bathed the surroundings forest in a foreboding light (not to mention that dwarves were a very loud race and had absolutely no concept of _stealth_ ). To his horror, Bilbo was among the dwarves tied up by large grey beings that had to be the ugliest things he had seen in a long time.

However, the hobbit was actually doing his best to save his comrades. Sly always believed into playing to one's strengths and one of the hobbit's strengths was talking. As Bilbo delayed the trolls from their meal, Sly quietly made his way behind the piled-up dwarves and began to untie them from bags and bonds. But not before using his cane to snag a small piece of metal from the loincloth of one beast that had caught his eye. He had to smack a few of them (mainly Fili and Kili) in the back of the head to get them to shut up when they yelled upon noticing him (because seriously, stealth was not a strong-suit for dwarves). Just as he freed Thorin, a familiar voice boomed "THE DAWN SHALL TAKE YOU ALL."

The raccoon looked up to see that the grey wizard had _cracked a freaking huge boulder in half_ to let the sunlight through and before his eyes, the ugly brutes were turned to stone.

As Gandalf smugly observed his work, Thorin approached. "Where have you been?"

"Looking ahead and providing answers."

"And what brought you back?"

"Looking behind. Still you are all in one piece."

"No thanks to your burglars." Thorin noted coolly, causing Sly to shoot him a disbelieving glare. _What an ungrateful ass!_ Gandalf merely quirked an eyebrow.

"At least Bilbo had the nerve to play for time. None of the rest of you thought of that. I also didn't see you untying yourselves."

Turning back to the statues and ignoring Thorin's chastised expression, Gandalf observed that they must have come from down from the Ettenmoors which led Thorin to observe that the mountain trolls ( _So that's what they were_ , Sly noted) must have had a cave nearby.

 **This is where I shall leave it for now as it is getting rather long. I know I am a little late in when I said to would upload this next chapter but I have to say that this section was a b****h to write. That, and life has been happening and me being caught up in it. On a side note, I decided to give Clockwerk a name (since he probably wouldn't have been called that originally) and "Bubo" is part of the latin name for horned owls (the -phet part seems to be common with ancient Egyptian names). I have not seen many other names for him and I am fairly sure that I am the first to give him this one. Anyway, the next chapter shall be released ASAP (I give no promises as to dates however) and please leave reviews! Also make sure to check out some of my other stories.**


	8. Chapter 6

**Me: Hello again!**

 **Sly: What the heck?**

 **Me: What?**

 **Sly: You forgot to include me in the intro of the last chapter! No hellos or anything. So rude.**

 **Me: Oh, but I thought you were annoyed by them.**

 **Sly: Just admit you forgot.** ** _Scoffs_**

 **Me: Alright fine but I have so much going on in life that I was over the moon just to have some time to write!**

 **Sly: No excuses, I wanna get home so hurry up!**

Disclaimer: I do not own anything from the Sly Cooper or the Hobbit.

* * *

Chapter 6- Always be prepared to run

As the unlikely group searched for the troll's lair, Sly got the whole story from Bilbo on how he and the dwarves had been waylaid by the brutes. Apparently, Fili and Kili had noticed that some of their ponies had gone missing and, spotting the large fire nearby, had sent poor Bilbo to investigate since he was a "burglar". Upon finding the horses (Shadow was unfortunately included) Bilbo had managed to free them but was captured in the process. As the horses ran off, the dwarves had charged in to save the hobbit. Which had not gone well.

Anyway, everyone was alive and well if not happy (Sly was still a little irked at Thorin's attitude). After a few minutes of searching, they came upon a cave with a horrible smell coming from its interior. However, the entrance seemed to be blocked by a large wooden door. "Troll work" snorted Thorin. "This should be no problem. Bofur, Bombur, Nori, get to it!"

Though they tried forcing the door, breaking it and even trying to pick the lock (Sly had to hide a grimace when he saw the shoddy pieces of metal Nori called lockpicks) it would not budge. Just as Thorin himself had finished shoving against it, Sly decided that enough was enough.

"I think this might help." With a smirk, Sly brought out the key which he had nabbed from one of the trolls. Snarling, the dwarf king snatched it and put it into the lock, causing the door to swing forward to reveal a damp cave. The smug raccoon followed the other dwarves inside while Bilbo remained outside. Unlike the young Baggins, Sly was used to unpleasant smells and angry glares so he could handle the troll aroma along with the grumpy glares from his dwarf companions.

Upon entering, the group found open chests filled with coins and riches scattered about. "Seems a shame to leave it lying around" Bofur observed casually "Anyone could take it." Sly, having already pocketed some of it to satisfy his kleptomania, merely nodded.

* * *

As Bofur and the Ri brothers set about burying the treasure ("We're simply making a long-term deposit!"), Sly began to wander outside before he noticed Gandalf and Thorin having an argument (yet again) about weapons. As he ambled over to take a look at the swords, he suddenly froze. For, amongst the webbed and dusty swords and daggers, he found something else that he hadn't expected to see in this realm.

A cane. A Cooper cane. A freaking, silver Cooper Cane.

Both king and wizard stopped mid argument as the thief reverently drew it from the rack. Once clean and brought out into the sunlight, the Cooper gasped. Unlike other Cooper canes which usually had some element of gold in them, this cane was a silvery white and seemed to gleam with a light of its own. Despite its length of four feet, it was also the lightest Cooper cane Sly had come across.

"Mithril" Thorin whispered reverently. "Aye" said Balin who had waited outside with Bilbo "Either from Moria or the north. But what a strange sha-?" the old dwarf had begun to say until he remembered the weapon Sly always had with him and was strapped to his back at this moment. The advisor filed the information away for now but would not forget it.

* * *

As Sly examined the cane, Gandalf presented Bilbo a small sword of Elvish make to use for his own protection. He was snapped out of his musing by a yell of "Thieves, fire, murder!"

He just managed to jump out of the way to avoid being run over by- wait a minute, were those rabbits? Pulling a sleigh? The man driving said sleigh looked similar to Gandalf yet wore robes of brown and seemed… less than concerned when it came to hygiene. _Please tell me those are not bird droppings in his hair_ Sly mentally begged.

"Radagast! Radagast the brown." Gandalf greeted the new arrival warmly. "What on earth are you doing here?"

"I was looking for you Gandalf I- I say is that Slytunkhamen?" Radagast suddenly broke off and began to circle the startled raccoon. "Well I must say, you look a good deal younger but what is that horrid ensemble you are wearing?"

Just as Sly began to feel rather offended (he was quite proud of his fashion sense thank you very much), Gandalf managed to pull the other wizard away to hear the reason why he had been looking for Gandalf in the first place.

"Yes Mr. Cooper" said a young voice behind him "what is that horrid ensemble you're wearing?" Rolling his eyes, Sly turned around to face a grinning Fili and Kili who were in the midst of sharpening their weapons. "What's wrong with it?"

At this, the brothers raised their eyebrows. "For starters, aren't thieves supposed to _blend in_? Yet you're wearing a royal blue hat and shirt with a bright yellow belt? Besides, you don't have any armor on. Where's your protection?"

Sly merely flicked his cap, smirking, and replied "I don't need it because I'm too good at what I do. You certainly didn't hear me on our little, shall we call it a _rescue mission_ my fair damsels, and you certainly didn't hear me take these." He dangled two small bags which had been filled with coins from the troll trove. Snickering as the two frantically searched themselves, Sly enquired "Your ensemble seems to be somewhat lacking if little old me can keep picking you blind." Tossing the bags back to the resigned duo, he did note that his own clothes _were_ starting to look a little worn.

As if to add to injury, they were about to endure even more abuse. For having a gigantic mutant wolf-thing jump on you didn't help your clothes. At all. Luckily, having a band of armed dwarves with you helps increase your survival if not that of your clothing. Shoving the beast off, Sly caught his breath and stared at it, ignoring the two large rips across the front of his shirt.

"Wargs!" Cried Nori. "Who have you told?" Asked Gandalf, who had come back with Radagast. "No one" Thorin answered curtly. "Who did you tell?!" Gandalf thundered. "No one I swear!"

"You are being hunted." Gandalf replied solemnly. "No, they were sending large dogs as a birthday present." Sly snarked. Before anyone could retort, more howls sounded nearby. "I'll draw them off!" Radagast volunteered crisply. Before anyone could say anything, he hurried over to his sleigh and ushered his rabbits onward. As he did so, the party started to run in a different direction and left the forest to come upon a field filled with boulders. They bolted behind the first boulder and as they hid, Sly whispered to Bilbo, "It's always best to be prepared to run in our line of business!"

 **See you next chapter! As always, please leave reviews!**


	9. Chapter 7

Chapter 7- Look out for your team

 **Me: I HAVE RETURNED**

 **Sly: I thought you died**

 **Me: Close, exams almost did me in**

 **Sly: Stop with the whining and let's get this show on the road!**

 **Me: Fine** ** _mutters_** **you impatient jerk; Disclaimer- I do not own anything/anyone from Middle Earth or the Sly Cooper universe, please read and review and I hope you enjoy**

There they were, Thorin and company hiding behind a large boulder with the sounds of wargs surrounding them. Peeking around, Sly saw Radagast being chased by wargs bearing ugly two-legged creatures that he could not name. "Orcs" hissed Thorin, unknowingly answering Sly's unspoken questions. With that, he waved for the company to move to the next boulder.

However, they moved too soon, for some of the rear guard of the orc party spotted them and rushed forward. Sly grabbed Bilbo's collar and yanked him into the shadows of the nearest boulder and gripped his cane. As the enemy approached, Kili began firing arrows and yelled "Where is Gandalf?" Sly looked around. Sure enough, the grey traveler was nowhere to be seen.

"He's abandoned us!" Dwalin snapped.

"This way you fools!" Gandalf's voice came from a strangely shaped boulder. Sly, towing Bilbo along, got to the boulder first and found the opening to a tunnel. Shoving Bilbo down into it, he prepared to jump in after him when he saw that Kili was dangerously close to being cut down by a warg. Acting quickly, Sly jumped in front of the young dwarf and threw a flash-bomb from his leg pouch, blinding the orc and allowing him to shove Kili into the hole.

Looking up, he saw Thorin give him a bewildered look, before nodding and entering the tunnel after cutting down a warg and its rider who had gotten too close. But just as Sly prepared to enter the tunnel, yet another orc came up behind him. On reflex, he raised his cane to defend himself. However, wood doesn't always hold up well against steel and with a resounding snap, his father's cane broke in half. With no time to react, Sly quickly scrambled down the hole to the rest of the company, just as the sound of a hunting horn and horse hooves thundered on the ground above them and the wargs snarls changed to shrieks and screams.

Suddenly, an orc fell down into the tunnel with them, an arrow in its throat. Thorin plucked the arrow out, then threw it on the ground in disgust. "Elves" he spat at Gandalf. Before Gandalf could reply, Dwalin called out "I cannot see where the path leads, do we follow it?" No longer able to contain his temper, Sly hissed "No, let's just go back up and say hello to the orcs shall we?" Ignoring the raccoon's sarcasm, Thorin nodded at Dwalin to lead the way with Sly numbly following along and not noticing Bilbo's concerned look. All he could think about was his father's cane, the cane that had served him so well on all of his adventures, the cane that his heritage and the cane that was the last reminder of a man who had shaped Sly's entire life before that fateful day all those years ago.

* * *

Brilliant sunshine pierced Sly's vision, snapping him out of his bleak reverie and after a moment of blinking, gasped at the sight before him. He had been many places in his world, but he had never seen a city that so completely managed to encompass healing and safety. The wooden city was nestled on a hillside with cascading waterfalls coming from the pavilions set upon the cliff tops. "The valley of Imraldis" Gandalf announced. "Rivendell…" he heard Bilbo murmur in awe.

"This was your plan all along" Thorin snarled at Gandalf "to see refuge with our enemy."

The grey wizard gave the dwarf a stern look. "The only ill-will to be found in this valley is that which you bring yourself. We have questions that need answers if you recall."

The motley group wearily crossed a large stone bridge that led to an elaborate stairway leading up to the city which was guarded by two imposing statues of tall armored figures. "Mithrandir" a voice called out. Sly looked up to see a tall figure coming down the stairs addressing Gandalf.

"Ah, Lindir! We must speak with Lord Elrond."

"My lord Elrond is not here."

"Not here? Where is he?"

Before Lindir could answer, the same hunting horns Sly had heard earlier rang out from behind. The company turned to behold a large group of horses bearing fair riders approaching them.

"Close ranks!" Thorin yelled. Bofur yanked Bilbo into the circle the dwarves had formed and raised his axe. While the riders surrounded the rest of the company, Sly observed them from where he stood near Gandalf. _These must be the elves that Bilbo and Thorin have mentioned_. They had a sort of ethereal grace that some might consider unsettling. Right now, he was too weary to be bothered. Also, for some reason, his left shoulder had begun to sting.

The thief's attention was diverted as one of the elves dismounted and strode towards them. "Lord Elrond" replied the grey wizard with a short bow. Elrond and Gandalf proceeded to have a short discussion in some foreign language Sly couldn't begin to understand before the warrior addressed the rest of the company.

"Strange for orcs to come so near to our borders." He remarked casually, tossing what Sly recognized as an Orc sword to Lindir.

"Well that may have been us" Gandalf admitted sheepishly. Thorin came to the front of the company and glared up at Elrond.

"Welcome to Rivendell, Thorin son of Thrain. You have your grandfather's bearing."

"Funny, he made no mention of you." Thorin replied frostily. The raccoon had to hold back an enormous eyeroll at the dwarf's antics as the elven leader turned to him.

"Young Cooper. You are also welcome to Rivendell."

As he nodded, Sly suddenly found himself completely exhausted. Just as vision began to go black, he heard Bilbo calling his name in concern and he knew no more.

 **Me: Rather short but more is coming!**

 **Sly: Wha-, WHY WOULD YOU DO THAT? MY DAD'S CANE?**

 **Me: *backing away nervously* Don't worry, everything will be alright! *runs in opposite direction***


	10. Chapter 8

I am back! Sorry, my muse took me in a different direction for a bit. But I swear I will finish this. Fair warning though, I start rotations this week so I may not be able to write for a few months.

Sly: DAMMIT WHEN ARE YOU GOING TO FINISH THIS? HOW MUCH MORE ARE GOING TO TORTURE ME?

Me: Sorry! Life be busy and you may be happier with what is about to happen.

Sly: Unlikely.

Disclaimer: I do not own any characters/settings from either the Sly Cooper or Hobbit universes.

* * *

He woke slowly, the blackness gradually fading to light until he regained awareness of his surroundings. The thief found himself in a bright room; it was as if shadows were banned from even existing in this place. He was on a sort of couch, covered with a comfortable blanket. Sitting up, he found his arm bandaged. Suddenly, he remembered the events leading to the injury and his bright mood dimmed. His cane...

Before his thoughts could turn to dark, three familiar figures burst into the room.

"Sly! You're finally awake." Bilbo happily regarded his friend before taking in his down-hearted expression.

Not noticing, Fili and Kili shouldered their way past the diminutive figure with broad grins. "Looks like you had a nice nap." Kili chimed in, "We thought we were going to have to kiss you awake after sleeping for a whole day." Finally noticing his demeanor, the two stopped. "What's up?"

"Do you... Have you guys seen... what's left of my cane?" Sly asked slowly, fighting against the pain of losing his heirloom. To his astonishment, his three visitors began smiling.

"Come down to breakfast." Bilbo said gently. "We have it down there."

Befuddled at their sudden merriment, Sly slowly followed them down to an dining hall where the rest of the company were gathered around a long wooden table filled with platters of food, though he noticed that none of it was meat. He grabbed a seat next to Bofur and snagged a roll to nibble on. Thorin, who had been sitting at the head of the table, walked over to the thief with a long cloth-covered bundle and gruffly cleared his throat.

"Here, young Cooper. You looked lost without it. Bofur is good at carving things and the elves have wood to spare." With that, Thorin began to mutter under his breath about the thrice cursed elves who loved wood more than creatures of flesh and blood and where they could shove said wood. Paying no mind, Sly unwrapped the bundle and gaped.

It was his cane. Whole, complete. Reverently, he lifted it up and balanced it on his hand. He worked his jaw, trying to say something. Finally he managed to utter a broken "Thank you."

The rest of the company looked sheepish yet happy. Thorn grunted. "Well, you used it to save mine nephew so you must need it."

Kili looked affronted. "I am quite capable of looking after myself, thank you very much." Dwalin came up behind him and whacked him on the back of the head.

"Show some gratitude." He grunted. Fili slung an arm around his younger brother, "Yes, Kili. Show the fuzzy man some gratitude."

Pulling himself together, Sly grinned. "Anytime, my fair damsel." His fingers continued to caress his cane as Kili spluttered in outrage whilst the others roared in laughter. He finished breakfast with the others then got up.

"And where are you going, laddie? I just spent hours carving that stick for ya and you're already going back into hiding." Bofur complained good naturedly. Smirking, Sly responded, "I have good reason to hide. I'm filthy so I was gonna go for a bath."

Kili sniffed. "Baths are overrated. We are perfectly fine with a little bit of good, healthy earth."

Leaving them to argue over baths, the raccoon made his way through the house, admiring the scenery.

* * *

"Sir, are you looking for something?" The thief whirled around to see a blonde elven maiden looking at him curiously. No doubt she had never seen anyone like him.

"Um, yes. I was hoping somewhere I could clean up."

"Oh, right this way." He was led to a room taken up almost entirely filled with a large stone pool filled with hot water. "Soap and scrub brushes are along the wall over there." The girl pointed to them. "I can't help but notice your raiment looks worn. I can bring you some new ones if you like."

Flashing her a winning smile, "That would be great. Thank you. But I have no way to pay for them..."

Blushing, the girl stammered. "Please think nothing of it." Before she rushed off. Once she was gone, he warily regarded the tub. He wasn't a very good swimmer. However, stepping in, he found it only went up to his mid-calves. Satisfied, he cleaned up and enjoyed the warmth of the bath.

* * *

A short while later, he emerged from the chamber, feeling refreshed. On the outside bench, he found a tunic and pulled it on to find it had a perfect fit. It was not his normal royal blue but a dark blue, tight fitting and so soft he had to stop himself from stroking it. It also had a hood which he mused may be helpful to cover his relatively bright peasant's cap even though they had somehow also changed the color of the head-piece as well. Looking back at the bench, he found that the maid had also left his belt (which had been repaired and polished) and his boots which had also been covered in the same dark material.

Dressed, he made his way out into the fresh air and ran his hand through his head-fur. He heard giggling. Out of the corner of his eye, could see a small group of elven maids peeking around a corner at him, blushing madly. He shot them a grin and they ran off, still giggling.

"But-, but that's not fair!" A familiar voice spluttered behind him. Kili had watched the whole scene with disbelief. "You're covered in fur! What in the name of Mordor do they see in _you_."

"What can I say? Girls just flock to me." He waltzed off, leaving the dwarf in stunned disbelief.

* * *

He ambled through the city, admiring its beauty. He strolled along its paths and gardens. Seeing the sun begin to set, he decided to return to the rest of the company. Before he could do so, however, a regal voice murmured.

"Young Cooper." Whirling around, Sly beheld a blonde woman garbed in white robes. She seemed ethereal, here yet observing from a world far away. She glowed faintly with an inner light and every single sense he possessed screamed at him not to trifle with this mysterious figure. Her gray eyes studied him intently.

He quickly settled his features into the bland politeness of his patented poker face, trying to hide his unease and awe. The woman smiled slightly. Turning, she gestured. "Come, we have much to discuss."

* * *

AN: A Cliffie! Mwahaha! Anyway, are you happy now? *Looks around to see Sly in a corner hugging his cane crying* I'll take that as a yes. Anyway, I'll get the next part of this wonderful tale out asap. Happy days until then :)


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